# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Ris445
_database_code_depnum_ccdc_archive 'CCDC 2492505'
loop_
_audit_author_name
_audit_author_address
'Dmitry Vinogradov'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2025-10-01 deposited with the CCDC.	2025-11-26 downloaded from the CCDC.
;
_audit_creation_date             2024-09-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 H3 N9 O3, C2 H6 O S'
_chemical_formula_sum            'C7 H9 N9 O4 S'
_chemical_formula_weight         315.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C7 H9 N9 O4 S'
_chemical_oxdiff_usercomment     Ris445
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   18.0728(2)
_cell_length_b                   9.94200(10)
_cell_length_c                   7.11510(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.4250(10)
_cell_angle_gamma                90
_cell_volume                     1276.16(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12788
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.2880
_cell_measurement_theta_min      4.9070
_shelx_estimated_absorpt_T_max   0.838
_shelx_estimated_absorpt_T_min   0.412
_exptl_absorpt_coefficient_mu    2.626
_exptl_absorpt_correction_T_max  0.840
_exptl_absorpt_correction_T_min  0.441
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.129a (Rigaku Oxford Diffraction, 2024)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.641
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             648
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.0349
-1 0 0 0.0339
0 0 -1 0.1165
0 0 1 0.2918
0 -1 0 0.1985
0 1 0 0.1676
1 -1 -1 0.0902
4 -4 -3 0.0875
6 4 -3 0.0847
-6 4 -3 0.0799

_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.07
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0000 0.0001 -0.0006 -0.0739 -0.0048 0.0425
-1.0000 -0.0001 0.0006 0.0739 0.0048 -0.0425
-0.0007 0.0007 -1.0000 0.1190 -0.0008 0.1814
0.0007 -0.0007 1.0000 -0.1190 0.0008 -0.1814
-0.0017 -0.9997 -0.0014 0.0072 -0.1547 -0.0052
0.0017 0.9997 0.0014 -0.0072 0.1547 0.0052
0.9977 -0.9989 -1.0020 0.0523 -0.1602 0.2187
3.8435 -4.2383 -3.2227 0.1283 -0.6770 0.7247
5.7040 4.1722 -2.8443 -0.1126 0.6157 0.7799
-5.8528 3.8878 -2.7335 0.7312 0.6270 0.2686

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            17412
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.152
_diffrn_reflns_theta_min         2.449
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -164.00 -70.50   0.55    0.40    --  -93.75-130.00-123.00  170
  2  ω   -116.00 -70.90   0.55    0.10    --  -44.92-130.00-123.00   82
  3  ω   -117.00 -63.65   0.55    0.10    --  -44.92-140.00  62.00   97
  4  ω    -97.00 -21.65   0.55    0.10    --  -44.92 140.00 122.00  137
  5  ω    -51.00 -20.75   0.55    0.40    --  -93.75  45.00 150.00   55
  6  ω   -117.00 -19.65   0.55    0.10    --  -44.92 -77.00-120.00  177
  7  ω     43.00 144.20   0.55    0.40    --  115.25 -86.00-160.63  184
  8  ω     44.00 114.40   0.55    0.40    --  115.25-130.00-123.00  128
  9  ω     45.00 110.45   0.55    0.40    --  115.25-125.00   0.00  119
 10  ω     45.00 110.45   0.55    0.40    --  115.25-125.00   0.00  119
 11  ω     45.00  84.05   0.55    0.40    --  115.25-125.00  60.00   71
 12  ω     43.00 122.20   0.55    0.40    --  115.25-140.00  62.00  144
 13  ω     82.00 108.40   0.55    0.40    --  115.25-125.00 150.00   48
 14  ω     45.00 110.45   0.55    0.40    --  115.25-125.00 150.00  119
 15  ω     43.00 102.95   0.55    0.10    --   44.92-140.00  62.00  109
 16  ω     43.00  72.15   0.55    0.40    --  115.25 -95.00-120.00   53
 17  ω     43.00 103.50   0.55    0.40    --  115.25 -95.00-150.00  110
 18  ω     81.00 110.15   0.55    0.40    --  115.25-125.00 -30.00   53
 19  ω     64.00 104.15   0.55    0.40    --  115.25-102.00   3.92   73
 20  ω     43.00  94.70   0.55    0.40    --  115.25 -77.00  60.00   94
 21  ω     53.00  79.40   0.55    0.40    --  115.25 -77.00 -60.00   48
 22  ω     45.00  69.75   0.55    0.40    --  115.25 -61.00 -60.00   45
 23  ω     47.00  73.40   0.55    0.40    --  115.25 -77.00 -90.00   48
 24  ω     76.00 100.75   0.55    0.40    --  115.25 -77.00-150.00   45
 25  ω     43.00  69.95   0.55    0.40    --  115.25 -61.00-150.00   49
 26  ω     43.00  69.95   0.55    0.40    --  115.25 -61.00-120.00   49
 27  ω    -32.00  26.30   0.55    0.10    --   44.92 -19.00  90.00  106
 28  ω     89.00 177.00   0.55    0.40    --  115.25  77.00 120.00  160
 29  ω     97.00 177.30   0.55    0.40    --  115.25  45.00  90.00  146
 30  ω     96.00 177.40   0.55    0.40    --  115.25  61.00  30.00  148
 31  ω    152.00 177.30   0.55    0.40    --  115.25  61.00  30.00   46
 32  ω     97.00 177.30   0.55    0.40    --  115.25  45.00 -60.00  146
 33  ω    131.80 178.00   0.55    0.40    --  115.25  15.00 -90.00   84
 34  ω     91.00 145.45   0.55    0.40    --  115.25  15.00-120.00   99
 35  ω    103.00 162.95   0.55    0.40    --  115.25  30.00-180.00  109
 36  ω     40.00 177.50   0.55    0.40    --  115.25   0.00-120.00  250
 37  ω     83.00 109.40   0.55    0.40    --  115.25   0.00-120.00   48
 38  ω    140.00 166.40   0.55    0.40    --  115.25 125.00  60.00   48
 39  ω     85.00 173.00   0.55    0.40    --  115.25 140.00 122.00  160
 40  ω    116.00 142.40   0.55    0.40    --  115.25 125.00 -30.00   48
 41  ω     92.00 177.25   0.55    0.40    --  115.25 130.00 -51.00  155
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0739891000
_diffrn_orient_matrix_UB_12      -0.0069228000
_diffrn_orient_matrix_UB_13      -0.1189346000
_diffrn_orient_matrix_UB_21      -0.0047801000
_diffrn_orient_matrix_UB_22      0.1547106000
_diffrn_orient_matrix_UB_23      0.0008989000
_diffrn_orient_matrix_UB_31      0.0423682000
_diffrn_orient_matrix_UB_32      0.0053499000
_diffrn_orient_matrix_UB_33      -0.1813889000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2699
_reflns_number_total             2756
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.129a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.129a 64-bit (release 29-06-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.129a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2756
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0392
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0662P)²+0.6893P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1085
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.32104(6) 0.24725(12) 0.49034(18) 0.0259(3) Uani 1 1 d . . . . .
N2 N 0.25822(7) 0.26196(13) 0.5417(2) 0.0199(3) Uani 1 1 d . . . . .
O3 O 0.21528(6) 0.14049(11) 0.57529(18) 0.0228(3) Uani 1 1 d . . . . .
N4 N 0.14663(7) 0.18023(13) 0.6285(2) 0.0207(3) Uani 1 1 d . . . . .
C5 C 0.14621(8) 0.31206(15) 0.6286(2) 0.0171(3) Uani 1 1 d . . . . .
C6 C 0.08148(8) 0.38727(15) 0.6825(2) 0.0167(3) Uani 1 1 d . . . . .
N7 N 0.08053(7) 0.51995(13) 0.68529(19) 0.0183(3) Uani 1 1 d . . . . .
N8 N 0.01173(7) 0.54643(13) 0.74318(19) 0.0186(3) Uani 1 1 d . . . . .
H8 H -0.0027(14) 0.633(3) 0.755(3) 0.032(6) Uiso 1 1 d . . . . .
C9 C -0.02430(8) 0.43143(16) 0.7718(2) 0.0193(3) Uani 1 1 d . . . . .
H9 H -0.0722(14) 0.430(2) 0.807(3) 0.030(6) Uiso 1 1 d . . . . .
N10 N 0.01797(7) 0.32685(13) 0.73480(19) 0.0188(3) Uani 1 1 d . . . . .
C11 C 0.21495(8) 0.36625(15) 0.5765(2) 0.0174(3) Uani 1 1 d . . . . .
C12 C 0.24006(8) 0.50562(15) 0.5602(2) 0.0172(3) Uani 1 1 d . . . . .
N13 N 0.19928(7) 0.58197(14) 0.42257(19) 0.0209(3) Uani 1 1 d . . . . .
N14 N 0.18894(7) 0.70268(14) 0.46367(19) 0.0223(3) Uani 1 1 d . . . . .
N15 N 0.17302(9) 0.81114(16) 0.4813(2) 0.0328(4) Uani 1 1 d . . . . .
N16 N 0.29732(7) 0.54111(13) 0.66382(19) 0.0201(3) Uani 1 1 d . . . . .
O17 O 0.31625(6) 0.67278(12) 0.62936(18) 0.0239(3) Uani 1 1 d . . . . .
H17 H 0.3573(17) 0.682(3) 0.712(4) 0.047(7) Uiso 1 1 d . . . . .
O18 O 0.56370(6) 0.22394(11) 0.66548(15) 0.0193(2) Uani 1 1 d . . . . .
S19 S 0.54262(2) 0.37072(4) 0.63921(5) 0.01852(14) Uani 1 1 d . . . . .
C20 C 0.60981(10) 0.46537(17) 0.7798(3) 0.0261(4) Uani 1 1 d . . . . .
H20A H 0.6107(12) 0.431(2) 0.905(3) 0.026(5) Uiso 1 1 d . . . . .
H20B H 0.5967(13) 0.559(3) 0.771(3) 0.030(6) Uiso 1 1 d . . . . .
H20C H 0.6565(15) 0.451(3) 0.732(4) 0.038(6) Uiso 1 1 d . . . . .
C21 C 0.46509(9) 0.39543(17) 0.7792(2) 0.0224(3) Uani 1 1 d . . . . .
H21A H 0.4793(13) 0.364(2) 0.904(3) 0.026(5) Uiso 1 1 d . . . . .
H21B H 0.4542(13) 0.493(3) 0.784(3) 0.027(5) Uiso 1 1 d . . . . .
H21C H 0.4255(13) 0.347(2) 0.718(3) 0.029(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N2 1.2221(18) . ?
N2 O3 1.4628(17) . ?
N2 C11 1.331(2) . ?
O3 N4 1.3766(17) . ?
N4 C5 1.311(2) . ?
C5 C6 1.459(2) . ?
C5 C11 1.423(2) . ?
C6 N7 1.3193(19) . ?
C6 N10 1.3667(19) . ?
N7 N8 1.3589(18) . ?
N8 H8 0.91(3) . ?
N8 C9 1.337(2) . ?
C9 H9 0.92(2) . ?
C9 N10 1.326(2) . ?
C11 C12 1.465(2) . ?
C12 N13 1.411(2) . ?
C12 N16 1.284(2) . ?
N13 N14 1.252(2) . ?
N14 N15 1.125(2) . ?
N16 O17 1.3787(16) . ?
O17 H17 0.92(3) . ?
O18 S19 1.5169(11) . ?
S19 C20 1.7931(18) . ?
S19 C21 1.7840(17) . ?
C20 H20A 0.95(2) . ?
C20 H20B 0.97(3) . ?
C20 H20C 0.94(3) . ?
C21 H21A 0.96(2) . ?
C21 H21B 0.99(3) . ?
C21 H21C 0.95(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N2 O3 117.48(12) . . ?
O1 N2 C11 135.69(14) . . ?
C11 N2 O3 106.82(12) . . ?
N4 O3 N2 107.68(11) . . ?
C5 N4 O3 107.00(12) . . ?
N4 C5 C6 121.15(13) . . ?
N4 C5 C11 111.92(13) . . ?
C11 C5 C6 126.90(14) . . ?
N7 C6 C5 121.85(14) . . ?
N7 C6 N10 115.06(13) . . ?
N10 C6 C5 123.09(13) . . ?
C6 N7 N8 102.19(12) . . ?
N7 N8 H8 119.1(16) . . ?
C9 N8 N7 110.07(13) . . ?
C9 N8 H8 130.9(16) . . ?
N8 C9 H9 122.4(16) . . ?
N10 C9 N8 110.42(14) . . ?
N10 C9 H9 127.2(16) . . ?
C9 N10 C6 102.27(13) . . ?
N2 C11 C5 106.57(13) . . ?
N2 C11 C12 122.26(14) . . ?
C5 C11 C12 131.16(14) . . ?
N13 C12 C11 114.35(13) . . ?
N16 C12 C11 117.21(14) . . ?
N16 C12 N13 128.34(14) . . ?
N14 N13 C12 115.63(13) . . ?
N15 N14 N13 170.99(17) . . ?
C12 N16 O17 111.03(13) . . ?
N16 O17 H17 100.4(18) . . ?
O18 S19 C20 106.23(8) . . ?
O18 S19 C21 105.28(7) . . ?
C21 S19 C20 98.31(8) . . ?
S19 C20 H20A 108.0(14) . . ?
S19 C20 H20B 108.4(14) . . ?
S19 C20 H20C 108.2(16) . . ?
H20A C20 H20B 113.3(19) . . ?
H20A C20 H20C 109(2) . . ?
H20B C20 H20C 110(2) . . ?
S19 C21 H21A 107.2(14) . . ?
S19 C21 H21B 108.6(13) . . ?
S19 C21 H21C 105.8(14) . . ?
H21A C21 H21B 109.0(18) . . ?
H21A C21 H21C 115(2) . . ?
H21B C21 H21C 111(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N8 H8 N10 0.91(3) 1.95(3) 2.8452(18) 171(2) 2_556 yes
C21 H21B O18 0.99(3) 2.35(3) 3.334(2) 172.6(18) 2_656 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N2 O3 N4 -179.05(13) . . . . ?
O1 N2 C11 C5 178.70(18) . . . . ?
O1 N2 C11 C12 -1.6(3) . . . . ?
N2 O3 N4 C5 -0.01(16) . . . . ?
N2 C11 C12 N13 117.71(16) . . . . ?
N2 C11 C12 N16 -59.1(2) . . . . ?
O3 N2 C11 C5 -0.62(16) . . . . ?
O3 N2 C11 C12 179.09(13) . . . . ?
O3 N4 C5 C6 -178.84(13) . . . . ?
O3 N4 C5 C11 -0.39(18) . . . . ?
N4 C5 C6 N7 179.24(15) . . . . ?
N4 C5 C6 N10 -0.3(2) . . . . ?
N4 C5 C11 N2 0.67(18) . . . . ?
N4 C5 C11 C12 -179.00(15) . . . . ?
C5 C6 N7 N8 -179.59(13) . . . . ?
C5 C6 N10 C9 179.55(14) . . . . ?
C5 C11 C12 N13 -62.7(2) . . . . ?
C5 C11 C12 N16 120.48(18) . . . . ?
C6 C5 C11 N2 179.01(14) . . . . ?
C6 C5 C11 C12 -0.7(3) . . . . ?
C6 N7 N8 C9 0.07(17) . . . . ?
N7 C6 N10 C9 0.01(18) . . . . ?
N7 N8 C9 N10 -0.06(18) . . . . ?
N8 C9 N10 C6 0.03(17) . . . . ?
N10 C6 N7 N8 -0.05(18) . . . . ?
C11 N2 O3 N4 0.42(16) . . . . ?
C11 C5 C6 N7 1.0(2) . . . . ?
C11 C5 C6 N10 -178.47(15) . . . . ?
C11 C12 N13 N14 143.30(14) . . . . ?
C11 C12 N16 O17 177.87(12) . . . . ?
N13 C12 N16 O17 1.5(2) . . . . ?
N16 C12 N13 N14 -40.3(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.823
_oxdiff_exptl_absorpt_empirical_full_min 0.444
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Ris703
_database_code_depnum_ccdc_archive 'CCDC 2492507'
loop_
_audit_author_name
_audit_author_address
'Dmitry Vinogradov'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2025-10-01 deposited with the CCDC.	2025-11-26 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT089_Ris703              
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       5.76 Note  
RESPONSE: The positions and parameters of the thermal displacement of
hydrogens were found from the e-map. Since the X-ray data was collected using
Cu Kalpha radiation (dmin=0.772A), there are not enough nonequivalent
reflections in the Ewald sphere to increase the number of data.
;
_audit_creation_date             2024-12-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 H2 N9 O3, C H6 N3'
_chemical_formula_sum            'C6 H8 N12 O3'
_chemical_formula_weight         296.24
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C6 H8 N12 O3'
_chemical_oxdiff_usercomment     Ris703
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   3.83694(5)
_cell_length_b                   17.9329(2)
_cell_length_c                   16.51337(18)
_cell_angle_alpha                90
_cell_angle_beta                 94.2871(11)
_cell_angle_gamma                90
_cell_volume                     1133.06(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9000
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      78.6970
_cell_measurement_theta_min      4.9030
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.746
_exptl_absorpt_coefficient_mu    1.247
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.629
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.143a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.737
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             608
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0346
-2 1 0 0.1355
0 0 -1 0.0585
0 1 0 0.0091
0 -1 0 0.0028
1 -1 -9 0.0387
-2 3 4 0.1190

_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.01
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0002 -0.0015 1.0001 -0.0035 -0.0931 0.0082
-2.0005 0.9994 0.0009 0.0045 -0.0115 -0.8098
0.0002 0.0015 -1.0001 0.0035 0.0931 -0.0082
-0.0001 0.9997 0.0005 -0.0853 0.0024 -0.0096
0.0001 -0.9997 -0.0005 0.0853 -0.0024 0.0096
1.4206 -0.5873 -9.2197 0.0202 0.8670 0.4979
-2.2640 2.7086 4.4275 -0.1458 -0.4213 -0.8951

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12386
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.895
_diffrn_reflns_theta_min         4.932
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -103.00 -24.90   0.55    0.30    --  -44.89 149.00 -68.00  142
  2  ω   -117.00 -57.05   0.55    0.30    --  -44.89-149.00-115.00  109
  3  ω    -85.00 -11.85   0.55    0.30    --  -44.89 124.00 127.00  133
  4  ω     47.00 109.15   0.55    0.30    --   44.89-149.00-115.00  113
  5  ω   -164.00 -73.80   0.55    1.00    --  -93.75-124.00  48.00  164
  6  ω    -85.00 -22.85   0.55    1.00    --  -93.75 124.00 127.00  113
  7  ω   -150.00 -56.50   0.55    1.00    --  -93.75-149.00-115.00  170
  8  ω     96.00 177.95   0.55    1.00    --  115.25 124.00 127.00  149
  9  ω     45.00 110.45   0.55    1.00    --  115.25-124.00  48.00  119
 10  ω     79.00 167.00   0.55    1.00    --  115.25 149.00 -68.00  160
 11  ω     47.00 128.95   0.55    1.00    --  115.25-149.00-115.00  149
 12  ω    -27.00  32.95   0.55    0.30    --  -44.89  19.00-180.00  109
 13  ω   -117.00 -18.55   0.55    0.30    --  -44.89 -77.00 150.00  179
 14  ω   -105.00 -79.15   0.55    0.30    --  -44.89 -77.00 150.00   47
 15  ω     81.00 116.20   0.55    0.30    --   44.89  57.00 120.00   64
 16  ω     27.00  73.20   0.55    0.30    --   44.89  57.00 120.00   84
 17  ω     28.00  55.50   0.55    0.30    --   44.89  57.00 -60.00   50
 18  ω    -31.00  15.20   0.55    0.30    --   44.89 -19.00 150.00   84
 19  ω     27.00  52.85   0.55    0.30    --   44.89  57.00-180.00   47
 20  ω    -22.00   3.30   0.55    0.30    --   44.89 -19.00  90.00   46
 21  ω     64.00  91.50   0.55    0.30    --   44.89  57.00 -60.00   50
 22  ω     19.00  77.85   0.55    0.30    --   44.89  77.00-150.00  107
 23  ω    -97.00 -72.25   0.55    1.00    --  -93.75 -72.00 160.75   45
 24  ω    -98.00 -72.15   0.55    1.00    --  -93.75 -72.00 153.38   47
 25  ω    -96.00 -68.50   0.55    1.00    --  -93.75 -77.00 150.00   50
 26  ω   -102.00 -70.10   0.55    1.00    --  -93.75 -71.00 131.61   58
 27  ω   -114.00 -75.50   0.55    1.00    --  -93.75 -50.00-141.42   70
 28  ω    -99.00 -74.25   0.55    1.00    --  -93.75 -61.00-150.00   45
 29  ω    -96.00 -70.15   0.55    1.00    --  -93.75 -77.00-150.00   47
 30  ω   -114.00 -70.55   0.55    1.00    --  -93.75 -74.00 -76.02   79
 31  ω    -96.00 -70.15   0.55    1.00    --  -93.75 -72.00 166.22   47
 32  ω    -94.00 -69.80   0.55    1.00    --  -93.75 -73.00 124.19   44
 33  ω   -104.00 -77.05   0.55    1.00    --  -93.75 -46.00 171.79   49
 34  ω    -95.00 -69.15   0.55    1.00    --  -93.75 -77.00-180.00   47
 35  ω    -93.00 -68.25   0.55    1.00    --  -93.75 -77.00 -90.00   45
 36  ω   -153.00-127.15   0.55    1.00    --  -93.75 -73.00 124.19   47
 37  ω    -96.00 -70.15   0.55    1.00    --  -93.75 -73.00 100.75   47
 38  ω    -95.00 -69.15   0.55    1.00    --  -93.75 -77.00 120.00   47
 39  ω    -93.00 -68.25   0.55    1.00    --  -93.75 -77.00  90.00   45
 40  ω    -99.00 -74.25   0.55    1.00    --  -93.75 -61.00-180.00   45
 41  ω    -96.00 -70.15   0.55    1.00    --  -93.75 -74.00-169.21   47
 42  ω    -95.00 -69.70   0.55    1.00    --  -93.75 -73.00 178.25   46
 43  ω    -94.00 -68.70   0.55    1.00    --  -93.75 -76.00-163.15   46
 44  ω   -139.00-113.15   0.55    1.00    --  -93.75 -77.00  90.00   47
 45  ω    -94.00 -68.15   0.55    1.00    --  -93.75 -77.00-120.00   47
 46  ω    -99.00 -73.15   0.55    1.00    --  -93.75 -67.00  86.89   47
 47  ω   -101.00 -75.15   0.55    1.00    --  -93.75 -46.00 178.69   47
 48  ω    -95.00 -70.25   0.55    1.00    --  -93.75 -72.00 107.74   45
 49  ω    138.00 177.60   0.55    1.00    --  115.25  61.00  90.00   72
 50  ω    104.00 130.40   0.55    1.00    --  115.25  61.00  90.00   48
 51  ω     43.00  69.95   0.55    1.00    --  115.25 -61.00   0.00   49
 52  ω    141.00 166.30   0.55    1.00    --  115.25  30.00-150.00   46
 53  ω     56.00  97.25   0.55    1.00    --  115.25 -77.00  90.00   75
 54  ω     47.00  94.85   0.55    1.00    --  115.25 -95.00  60.00   87
 55  ω    136.00 171.20   0.55    1.00    --  115.25  77.00  60.00   64
 56  ω     43.00  69.95   0.55    1.00    --  115.25 -61.00-120.00   49
 57  ω    125.00 151.40   0.55    1.00    --  115.25  77.00 -90.00   48
 58  ω     74.00 110.85   0.55    1.00    --  115.25-125.00 -30.00   67
 59  ω     91.00 120.70   0.55    1.00    --  115.25  77.00 -90.00   54
 60  ω     43.00  70.50   0.55    1.00    --  115.25 -61.00-180.00   50
 61  ω     92.00 129.40   0.55    1.00    --  115.25  77.00  60.00   68
 62  ω    140.00 165.30   0.55    1.00    --  115.25  77.00-120.00   46
 63  ω     43.00  67.75   0.55    1.00    --  115.25 -61.00-150.00   45
 64  ω    114.00 160.20   0.55    1.00    --  115.25 125.00  90.00   84
 65  ω    138.00 164.40   0.55    1.00    --  115.25  77.00-180.00   48
 66  ω    103.00 177.25   0.55    1.00    --  115.25  30.00  30.00  135
 67  ω    132.00 176.00   0.55    1.00    --  115.25  30.00 -30.00   80
 68  ω     48.00 102.45   0.55    1.00    --  115.25 -77.00 150.00   99
 69  ω     95.00 119.75   0.55    1.00    --  115.25  77.00-180.00   45
 70  ω     90.00 115.85   0.55    1.00    --  115.25  77.00-120.00   47
 71  ω     44.00  87.45   0.55    1.00    --  115.25 -77.00  60.00   79
 72  ω     44.00  68.75   0.55    1.00    --  115.25 -77.00-120.00   45
 73  ω    135.00 167.45   0.55    1.00    --  115.25  61.00  60.00   59
 74  ω    148.00 174.95   0.55    1.00    --  115.25  30.00-180.00   49
 75  ω    142.00 167.30   0.55    1.00    --  115.25  15.00 120.00   46
 76  ω     96.00 128.45   0.55    1.00    --  115.25  61.00  60.00   59
 77  ω     97.00 122.85   0.55    1.00    --  115.25  61.00-120.00   47
 78  ω    103.00 132.70   0.55    1.00    --  115.25  61.00-180.00   54
 79  ω     94.00 121.50   0.55    1.00    --  115.25  77.00 150.00   50
 80  ω    150.00 178.05   0.55    1.00    --  115.25  61.00 120.00   51
 81  ω     98.00 140.35   0.55    1.00    --  115.25  30.00-180.00   77
 82  ω    132.00 161.15   0.55    1.00    --  115.25  30.00 -90.00   53
 83  ω     97.00 129.45   0.55    1.00    --  115.25  61.00 -90.00   59
 84  ω    128.00 154.40   0.55    1.00    --  115.25  45.00  60.00   48
 85  ω    143.00 172.70   0.55    1.00    --  115.25  77.00-150.00   54
 86  ω    119.00 145.40   0.55    1.00    --  115.25  45.00-150.00   48
 87  ω     54.00  78.75   0.55    1.00    --  115.25-125.00  90.00   45
 88  ω     96.00 121.85   0.55    1.00    --  115.25  77.00-150.00   47
 89  ω    121.00 147.40   0.55    1.00    --  115.25  61.00 120.00   48
 90  ω     79.00 103.75   0.55    1.00    --  115.25 -77.00   0.00   45
 91  ω     79.00 103.75   0.55    1.00    --  115.25 -77.00-150.00   45
 92  ω    137.00 175.50   0.55    1.00    --  115.25  61.00-150.00   70
 93  ω     97.00 132.20   0.55    1.00    --  115.25  61.00-150.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0448978000
_diffrn_orient_matrix_UB_12      -0.0853368000
_diffrn_orient_matrix_UB_13      -0.0036742000
_diffrn_orient_matrix_UB_21      0.0069608000
_diffrn_orient_matrix_UB_22      0.0024837000
_diffrn_orient_matrix_UB_23      -0.0931238000
_diffrn_orient_matrix_UB_31      0.4000255000
_diffrn_orient_matrix_UB_32      -0.0095810000
_diffrn_orient_matrix_UB_33      0.0082439000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.899
_reflns_Friedel_fraction_full    0.938
_reflns_Friedel_fraction_max     0.907
_reflns_number_gt                2328
_reflns_number_total             2351
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.143a 64-bit (release 25-10-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.143a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 1085 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(11)
_refine_ls_extinction_coef       0.0015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         2351
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0252
_refine_ls_R_factor_gt           0.0250
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0380P)²+0.4224P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0655
_refine_ls_wR_factor_ref         0.0657
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2596(4) 0.45582(8) 0.71151(8) 0.0180(3) Uani 1 1 d . . . . .
N2 N 0.4321(4) 0.47601(9) 0.64951(10) 0.0147(3) Uani 1 1 d . . . . .
N3 N 0.5846(5) 0.54265(10) 0.64506(11) 0.0181(4) Uani 1 1 d . . . . .
N4 N 0.7272(5) 0.54424(10) 0.57504(11) 0.0194(4) Uani 1 1 d . . . . .
N5 N 0.6730(5) 0.48043(10) 0.53380(11) 0.0175(4) Uani 1 1 d . . . . .
C6 C 0.4866(5) 0.43795(10) 0.58081(13) 0.0147(4) Uani 1 1 d . . . . .
C7 C 0.3547(5) 0.36337(11) 0.56333(12) 0.0145(4) Uani 1 1 d . . . . .
N8 N 0.3782(5) 0.31123(9) 0.62091(11) 0.0167(4) Uani 1 1 d . . . . .
O9 O 0.5178(4) 0.30686(8) 0.69005(9) 0.0218(3) Uani 1 1 d . . . . .
O10 O 0.1969(4) 0.24617(8) 0.58932(9) 0.0208(3) Uani 1 1 d . . . . .
N11 N 0.0825(5) 0.26128(10) 0.50994(10) 0.0191(4) Uani 1 1 d . . . . .
C12 C 0.1778(5) 0.32925(11) 0.49358(12) 0.0150(4) Uani 1 1 d . . . . .
C13 C 0.1038(5) 0.35686(11) 0.41071(12) 0.0145(4) Uani 1 1 d . . . . .
N14 N -0.0814(5) 0.31442(9) 0.35406(11) 0.0175(4) Uani 1 1 d . . . . .
C15 C -0.0783(6) 0.35634(12) 0.28833(13) 0.0178(4) Uani 1 1 d . . . . .
H15 H -0.188(9) 0.3462(17) 0.2345(19) 0.027 Uiso 1 1 d . U . . .
N16 N 0.0998(5) 0.41943(10) 0.30460(10) 0.0160(3) Uani 1 1 d . . . . .
H16 H 0.150(8) 0.4577(17) 0.2714(19) 0.024 Uiso 1 1 d . U . . .
N17 N 0.2222(5) 0.42100(10) 0.38377(10) 0.0157(4) Uani 1 1 d . . . . .
N18 N 0.7376(5) 0.56510(10) 0.36457(11) 0.0182(4) Uani 1 1 d . . . . .
H18A H 0.632(9) 0.5645(16) 0.315(2) 0.027 Uiso 1 1 d . U . . .
H18B H 0.688(9) 0.5319(18) 0.400(2) 0.027 Uiso 1 1 d . U . . .
C19 C 0.9498(5) 0.62209(11) 0.38327(12) 0.0160(4) Uani 1 1 d . . . . .
N20 N 1.0363(5) 0.66919(10) 0.32650(12) 0.0195(4) Uani 1 1 d . . . . .
H20A H 1.178(9) 0.7087(18) 0.341(2) 0.029 Uiso 1 1 d . U . . .
H20B H 1.000(9) 0.6557(19) 0.279(2) 0.029 Uiso 1 1 d . U . . .
N21 N 1.0806(5) 0.63206(11) 0.45953(11) 0.0201(4) Uani 1 1 d . . . . .
H21A H 0.985(9) 0.6071(17) 0.498(2) 0.030 Uiso 1 1 d . U . . .
H21B H 1.243(10) 0.6681(19) 0.466(2) 0.030 Uiso 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N2 1.311(2) . ?
N2 N3 1.335(2) . ?
N2 C6 1.354(3) . ?
N3 N4 1.316(2) . ?
N4 N5 1.340(3) . ?
N5 C6 1.333(3) . ?
C6 C7 1.451(3) . ?
C7 N8 1.332(3) . ?
C7 C12 1.430(3) . ?
N8 O9 1.227(2) . ?
N8 O10 1.436(2) . ?
O10 N11 1.378(2) . ?
N11 C12 1.307(3) . ?
C12 C13 1.463(3) . ?
C13 N14 1.364(3) . ?
C13 N17 1.326(3) . ?
N14 C15 1.321(3) . ?
C15 H15 0.97(3) . ?
C15 N16 1.339(3) . ?
N16 H16 0.91(3) . ?
N16 N17 1.356(2) . ?
N18 H18A 0.89(4) . ?
N18 H18B 0.86(3) . ?
N18 C19 1.328(3) . ?
C19 N20 1.323(3) . ?
C19 N21 1.332(3) . ?
N20 H20A 0.91(3) . ?
N20 H20B 0.83(4) . ?
N21 H21A 0.88(4) . ?
N21 H21B 0.90(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N2 N3 122.62(16) . . ?
O1 N2 C6 129.35(17) . . ?
N3 N2 C6 108.02(17) . . ?
N4 N3 N2 106.29(17) . . ?
N3 N4 N5 111.66(18) . . ?
C6 N5 N4 105.17(17) . . ?
N2 C6 C7 123.91(18) . . ?
N5 C6 N2 108.85(17) . . ?
N5 C6 C7 127.23(19) . . ?
N8 C7 C6 120.06(18) . . ?
N8 C7 C12 106.10(17) . . ?
C12 C7 C6 133.79(18) . . ?
C7 N8 O10 107.81(16) . . ?
O9 N8 C7 135.30(19) . . ?
O9 N8 O10 116.87(16) . . ?
N11 O10 N8 107.27(14) . . ?
C12 N11 O10 107.82(16) . . ?
C7 C12 C13 130.98(18) . . ?
N11 C12 C7 110.85(17) . . ?
N11 C12 C13 118.13(18) . . ?
N14 C13 C12 120.50(17) . . ?
N17 C13 C12 124.07(18) . . ?
N17 C13 N14 115.34(17) . . ?
C15 N14 C13 102.11(17) . . ?
N14 C15 H15 128.0(19) . . ?
N14 C15 N16 110.60(18) . . ?
N16 C15 H15 121.4(19) . . ?
C15 N16 H16 130(2) . . ?
C15 N16 N17 110.23(16) . . ?
N17 N16 H16 119(2) . . ?
C13 N17 N16 101.71(16) . . ?
H18A N18 H18B 120(3) . . ?
C19 N18 H18A 117(2) . . ?
C19 N18 H18B 122(2) . . ?
N18 C19 N21 120.27(19) . . ?
N20 C19 N18 120.56(19) . . ?
N20 C19 N21 119.17(19) . . ?
C19 N20 H20A 119(2) . . ?
C19 N20 H20B 117(2) . . ?
H20A N20 H20B 122(3) . . ?
C19 N21 H21A 118(2) . . ?
C19 N21 H21B 115(2) . . ?
H21A N21 H21B 127(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C15 H15 N3 0.97(3) 2.59(3) 3.177(3) 119(2) 2_464 yes
N16 H16 O1 0.91(3) 1.90(3) 2.808(2) 174(3) 2_564 yes
N18 H18A O1 0.89(4) 2.17(4) 3.033(2) 163(3) 2_564 yes
N18 H18B N5 0.86(3) 2.40(3) 3.206(3) 155(3) . yes
N20 H20A N14 0.91(3) 2.11(3) 3.007(3) 166(3) 3_655 yes
N20 H20B O1 0.83(4) 2.53(3) 3.100(2) 127(3) 2_664 yes
N20 H20B O9 0.83(4) 2.37(4) 2.924(2) 125(3) 2_564 yes
N21 H21A N4 0.88(4) 2.01(4) 2.889(3) 173(3) . yes
N21 H21B N11 0.90(4) 2.21(4) 3.087(3) 166(3) 3_655 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N2 N3 N4 -179.08(17) . . . . ?
O1 N2 C6 N5 179.19(18) . . . . ?
O1 N2 C6 C7 -0.1(3) . . . . ?
N2 N3 N4 N5 -0.2(2) . . . . ?
N2 C6 C7 N8 -43.9(3) . . . . ?
N2 C6 C7 C12 133.3(2) . . . . ?
N3 N2 C6 N5 0.2(2) . . . . ?
N3 N2 C6 C7 -179.12(19) . . . . ?
N3 N4 N5 C6 0.3(2) . . . . ?
N4 N5 C6 N2 -0.3(2) . . . . ?
N4 N5 C6 C7 179.0(2) . . . . ?
N5 C6 C7 N8 136.9(2) . . . . ?
N5 C6 C7 C12 -45.9(4) . . . . ?
C6 N2 N3 N4 0.0(2) . . . . ?
C6 C7 N8 O9 -7.3(4) . . . . ?
C6 C7 N8 O10 174.21(17) . . . . ?
C6 C7 C12 N11 -174.1(2) . . . . ?
C6 C7 C12 C13 8.3(4) . . . . ?
C7 N8 O10 N11 2.9(2) . . . . ?
C7 C12 C13 N14 -178.0(2) . . . . ?
C7 C12 C13 N17 5.7(3) . . . . ?
N8 C7 C12 N11 3.4(2) . . . . ?
N8 C7 C12 C13 -174.2(2) . . . . ?
N8 O10 N11 C12 -0.8(2) . . . . ?
O9 N8 O10 N11 -175.90(17) . . . . ?
O10 N11 C12 C7 -1.6(2) . . . . ?
O10 N11 C12 C13 176.41(17) . . . . ?
N11 C12 C13 N14 4.5(3) . . . . ?
N11 C12 C13 N17 -171.7(2) . . . . ?
C12 C7 N8 O9 174.8(2) . . . . ?
C12 C7 N8 O10 -3.7(2) . . . . ?
C12 C13 N14 C15 -177.35(19) . . . . ?
C12 C13 N17 N16 177.14(18) . . . . ?
C13 N14 C15 N16 0.5(2) . . . . ?
N14 C13 N17 N16 0.7(2) . . . . ?
N14 C15 N16 N17 -0.1(2) . . . . ?
C15 N16 N17 C13 -0.3(2) . . . . ?
N17 C13 N14 C15 -0.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.361
_oxdiff_exptl_absorpt_empirical_full_min 0.808
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Ris657
_database_code_depnum_ccdc_archive 'CCDC 2492506'
loop_
_audit_author_name
_audit_author_address
'Dmitry Vinogradov'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2025-10-01 deposited with the CCDC.	2025-11-26 downloaded from the CCDC.
;
_audit_creation_date             2025-06-05
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2025.05.31 svn.r86d253d1 for OlexSys, GUI svn.r7254)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 H5 K2 N9 O5'
_chemical_formula_sum            'C5 H5 K2 N9 O5'
_chemical_formula_weight         349.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C5 H N9 O3 K'
_chemical_oxdiff_usercomment     Ris657
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
K K 0.3868 1.0657 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9975(2)
_cell_length_b                   8.9440(2)
_cell_length_c                   11.0111(3)
_cell_angle_alpha                66.363(3)
_cell_angle_beta                 86.447(2)
_cell_angle_gamma                75.934(2)
_cell_volume                     611.90(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    19519
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      79.0860
_cell_measurement_theta_min      4.3430
_shelx_estimated_absorpt_T_max   0.811
_shelx_estimated_absorpt_T_min   0.285
_exptl_absorpt_coefficient_mu    7.298
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.524
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.44.112a (Rigaku Oxford Diffraction, 2025)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.896
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             352
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 -1 -1 0.0664
2 1 1 0.1558
0 -1 2 0.0240
0 5 5 0.0078
0 -5 -5 0.0175
4 4 0 0.1262
0 6 3 0.0078
-4 -3 0 0.0622
0 -5 0 0.0210
0 0 -6 0.0295

_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-2.0000 -1.0000 -1.0000 0.0206 -0.0651 0.4500
2.0000 1.0000 1.0000 -0.0206 0.0651 -0.4500
-0.0000 -1.0000 2.0000 0.0021 -0.4068 -0.1122
0.2807 5.1440 5.4316 0.9451 0.0745 -0.3181
-0.1661 -5.1326 -5.3929 -0.9531 -0.0752 0.2930
3.8184 3.8650 0.0309 0.0838 0.6581 -0.7482
0.1919 5.6855 2.9576 0.8660 0.4720 -0.1652
-4.4223 -2.5185 -0.3305 0.1256 -0.4321 0.8930
-0.1311 -5.1385 0.1873 -0.6078 -0.7940 -0.0119
0.0421 0.3410 -6.3615 -0.3610 0.8711 0.3329

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0630
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            30583
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.176
_diffrn_reflns_theta_min         4.387
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -79.00  26.05   0.55    1.00    --  -44.91  96.00  -9.00  191
  2  ω     -7.00  78.25   0.55    1.00    --   44.91 -96.00-118.00  155
  3  ω   -165.00 -85.25   0.55    5.00    --  -93.75 -96.00-118.00  145
  4  ω    -80.00 -22.80   0.55    5.00    --  -93.75  96.00  -9.00  104
  5  ω     44.00 103.95   0.55    5.00    --  115.25 -96.00-118.00  109
  6  ω    106.00 177.50   0.55    5.00    --  115.25  96.00  -9.00  130
  7  ω    -59.00 -30.95   0.55    1.00    --   12.00 158.00-154.54   51
  8  ω   -118.00 -26.70   0.55    1.00    --  -44.91 -57.00-180.00  166
  9  ω    -43.00  28.50   0.55    1.00    --  -44.91  38.00-180.00  130
 10  ω   -118.00 -26.70   0.55    1.00    --  -44.91 -57.00-180.00  166
 11  ω     19.00 117.45   0.55    1.00    --   44.91  77.00  30.00  179
 12  ω     19.00 117.45   0.55    1.00    --   44.91  77.00-180.00  179
 13  ω     34.00  92.85   0.55    1.00    --   44.91-125.00 -90.00  107
 14  ω     19.00 117.45   0.55    1.00    --   44.91  77.00  30.00  179
 15  ω     24.00 122.45   0.55    1.00    --   44.91  19.00 -60.00  179
 16  ω     27.00 117.20   0.55    1.00    --   44.91  57.00 -90.00  164
 17  ω     27.00 119.40   0.55    1.00    --   44.91  38.00   0.00  168
 18  ω     24.00 122.45   0.55    1.00    --   44.91  19.00 -60.00  179
 19  ω     19.00 117.45   0.55    1.00    --   44.91  77.00  60.00  179
 20  ω     17.00  41.75   0.55    1.00    --   48.00  88.00-154.86   45
 21  ω     16.00  40.75   0.55    1.00    --   48.00  91.00 -78.25   45
 22  ω     15.00  39.75   0.55    1.00    --   48.00  92.00  72.67   45
 23  ω     30.00 128.45   0.55    1.00    --   56.00  77.00-106.03  179
 24  ω     30.00 128.45   0.55    1.00    --   56.00  77.00-106.03  179
 25  ω     31.00 129.45   0.55    1.00    --   56.00  75.00  95.23  179
 26  ω     35.00 132.35   0.55    1.00    --   60.00  75.00 -25.28  177
 27  ω     35.00 132.35   0.55    1.00    --   60.00  76.00-132.57  177
 28  ω     39.00 137.45   0.55    1.00    --   64.00  74.00  25.11  179
 29  ω     39.00 137.45   0.55    1.00    --   64.00  74.00  25.11  179
 30  ω     40.00 137.35   0.55    1.00    --   64.00  72.00 -46.92  177
 31  ω     39.00 137.45   0.55    1.00    --   64.00  76.00 110.92  179
 32  ω   -140.00 -45.95   0.55    1.00    --  -68.00 -70.00 -20.06  171
 33  ω   -140.00 -45.95   0.55    1.00    --  -68.00 -70.00 -20.06  171
 34  ω   -140.00 -47.60   0.55    1.00    --  -68.00 -64.00 100.15  168
 35  ω   -140.00 -47.60   0.55    1.00    --  -68.00 -64.00 118.79  168
 36  ω   -140.00 -48.70   0.55    1.00    --  -68.00 -63.00 137.59  166
 37  ω   -145.00 -53.70   0.55    1.00    --  -72.00 -60.00  10.07  166
 38  ω   -145.00 -50.95   0.55    1.00    --  -72.00 -67.00-116.02  171
 39  ω     46.00 144.45   0.55    1.00    --   72.00  77.00-146.41  179
 40  ω   -145.00 -47.65   0.55    1.00    --  -72.00 -74.00-174.70  177
 41  ω   -145.00 -47.65   0.55    1.00    --  -72.00 -74.00-174.70  177
 42  ω   -145.00 -50.95   0.55    1.00    --  -72.00 -67.00-116.02  171
 43  ω   -149.00 -51.65   0.55    1.00    --  -76.00 -75.00   8.49  177
 44  ω   -149.00 -52.75   0.55    1.00    --  -76.00 -71.00  48.81  175
 45  ω   -149.00 -52.75   0.55    1.00    --  -76.00 -73.00-120.96  175
 46  ω   -153.00 -60.60   0.55    1.00    --  -80.00 -59.00  60.90  168
 47  ω   -153.00 -59.50   0.55    1.00    --  -80.00 -64.00  89.47  170
 48  ω   -153.00 -60.60   0.55    1.00    --  -80.00 -59.00  60.90  168
 49  ω    -93.00 -63.30   0.55    1.00    --  -80.00 -60.00 -22.03   54
 50  ω    -99.00 -62.70   0.55    5.00    --  -84.00 -66.00 128.82   66
 51  ω    -97.00 -70.60   0.55    5.00    --  -88.00 -72.00  53.68   48
 52  ω    -91.00 -64.60   0.55    5.00    --  -88.00 -76.00-125.42   48
 53  ω   -102.00 -69.55   0.55    5.00    --  -93.75 -73.00 -75.64   59
 54  ω   -105.00 -69.80   0.55    5.00    --  -93.75 -75.00 -29.16   64
 55  ω   -123.00 -68.55   0.55    5.00    --  -93.75 -77.00-150.00   99
 56  ω   -107.00 -69.60   0.55    5.00    --  -93.75 -73.00 162.96   68
 57  ω   -125.00 -76.60   0.55    5.00    --  -93.75 -61.00  30.00   88
 58  ω    -95.00 -70.25   0.55    5.00    --  -93.75 -74.00 -18.56   45
 59  ω   -146.00-119.60   0.55    5.00    --  -93.75 -74.00 -18.56   48
 60  ω   -163.00-136.60   0.55    5.00    --  -93.75 -77.00-150.00   48
 61  ω   -119.00 -75.55   0.55    5.00    --  -93.75 -58.00  -9.40   79
 62  ω    -94.00 -69.25   0.55    5.00    --  -93.75 -77.00  90.00   45
 63  ω    -95.00 -70.25   0.55    5.00    --  -93.75 -75.00 -41.78   45
 64  ω   -155.00-129.70   0.55    5.00    --  -93.75 -75.00 -41.78   46
 65  ω   -102.00 -72.30   0.55    5.00    --  -93.75 -70.00 -62.84   54
 66  ω   -160.00-134.70   0.55    5.00    --  -93.75 -70.00 -62.84   46
 67  ω   -103.00 -70.55   0.55    5.00    --  -93.75 -77.00  30.00   59
 68  ω    -97.00 -70.60   0.55    5.00    --  -93.75 -72.00-102.44   48
 69  ω   -130.00 -70.05   0.55    5.00    --  -93.75 -73.00 124.48  109
 70  ω    -96.00 -69.60   0.55    5.00    --  -93.75 -77.00-180.00   48
 71  ω     44.00  68.75   0.55    5.00    --  115.25 -77.00-120.00   45
 72  ω     48.00 109.05   0.55    5.00    --  115.25-125.00 -90.00  111
 73  ω    138.00 164.40   0.55    5.00    --  115.25  77.00  90.00   48
 74  ω     99.00 125.95   0.55    5.00    --  115.25  77.00  90.00   49
 75  ω     93.00 119.40   0.55    5.00    --  115.25  77.00-120.00   48
 76  ω    149.00 175.40   0.55    5.00    --  115.25  61.00 150.00   48
 77  ω     89.00 158.30   0.55    5.00    --  115.25  77.00 -60.00  126
 78  ω    138.00 174.30   0.55    5.00    --  115.25  77.00  60.00   66
 79  ω     98.00 124.40   0.55    5.00    --  115.25  61.00 150.00   48
 80  ω    130.00 174.00   0.55    5.00    --  115.25  45.00 120.00   80
 81  ω     98.00 141.45   0.55    5.00    --  115.25  45.00 -90.00   79
 82  ω     94.00 120.40   0.55    5.00    --  115.25  77.00  60.00   48
 83  ω     73.00  99.40   0.55    5.00    --  115.25-125.00 120.00   48
 84  ω    131.00 160.70   0.55    5.00    --  115.25  77.00 -30.00   54
 85  ω     48.00  82.10   0.55    5.00    --  115.25-125.00   0.00   62
 86  ω     85.00 109.75   0.55    5.00    --  115.25-125.00  60.00   45
 87  ω     90.00 126.30   0.55    5.00    --  115.25  77.00 -30.00   66
 88  ω    123.00 149.40   0.55    5.00    --  115.25  30.00 -30.00   48
 89  ω     57.00  83.40   0.55    5.00    --  115.25-125.00  60.00   48
 90  ω     69.00  95.40   0.55    5.00    --  115.25 -77.00-180.00   48
 91  ω    102.00 174.05   0.55    5.00    --  115.25  61.00   0.00  131
 92  ω     44.00  68.75   0.55    5.00    --  115.25 -61.00 -30.00   45
 93  ω     99.00 125.95   0.55    5.00    --  115.25  61.00  90.00   49
 94  ω    100.00 148.95   0.55    5.00    --  115.25  61.00-180.00   89
 95  ω    119.00 158.05   0.55    5.00    --  115.25  30.00 -90.00   71
 96  ω     44.00  87.45   0.55    5.00    --  115.25 -77.00 150.00   79
 97  ω    152.00 177.30   0.55    5.00    --  115.25  61.00  60.00   46
 98  ω    139.00 165.40   0.55    5.00    --  115.25  45.00 150.00   48
 99  ω     98.00 124.40   0.55    5.00    --  115.25  45.00 150.00   48
100  ω    147.00 173.95   0.55    5.00    --  115.25  77.00 120.00   49
101  ω     89.00 115.95   0.55    5.00    --  115.25  77.00 120.00   49
102  ω     90.00 171.40   0.55    5.00    --  115.25  77.00 -90.00  148
103  ω    141.00 167.40   0.55    5.00    --  115.25  30.00   0.00   48
104  ω     96.00 141.10   0.55    5.00    --  115.25 125.00  90.00   82
105  ω    106.00 132.40   0.55    5.00    --  115.25  30.00   0.00   48
106  ω     44.00  68.75   0.55    5.00    --  115.25 -77.00-150.00   45
107  ω     53.00  99.20   0.55    5.00    --  115.25 -77.00   0.00   84
108  ω     79.00 103.75   0.55    5.00    --  115.25 -95.00  90.00   45
109  ω    105.00 158.35   0.55    5.00    --  115.25  45.00-150.00   97
110  ω     46.00 110.35   0.55    5.00    --  115.25-125.00-180.00  117
111  ω     74.00 103.70   0.55    5.00    --  115.25 -95.00  60.00   54
112  ω     45.00  71.40   0.55    5.00    --  115.25-125.00 120.00   48
113  ω     69.00 101.45   0.55    5.00    --  115.25 -95.00   0.00   59
114  ω    147.00 173.40   0.55    5.00    --  115.25  77.00   0.00   48
115  ω     44.00  70.40   0.55    5.00    --  115.25 -61.00  90.00   48
116  ω     90.00 119.70   0.55    5.00    --  115.25  77.00   0.00   54
117  ω    152.00 177.30   0.55    5.00    --  115.25  77.00-180.00   46
118  ω     43.00  69.40   0.55    5.00    --  115.25 -61.00-180.00   48
119  ω    106.00 150.00   0.55    5.00    --  115.25  30.00-150.00   80
120  ω     98.00 138.15   0.55    5.00    --  115.25  61.00 -90.00   73
121  ω     47.00  71.75   0.55    5.00    --  115.25 -95.00  60.00   45
122  ω     89.00 115.40   0.55    5.00    --  115.25  77.00-180.00   48
123  ω    122.00 172.05   0.55    5.00    --  115.25  77.00  30.00   91
124  ω    141.00 166.30   0.55    5.00    --  115.25  61.00 -60.00   46
125  ω     99.00 130.35   0.55    5.00    --  115.25  61.00 -60.00   57
126  ω     91.00 117.40   0.55    5.00    --  115.25  77.00  30.00   48
127  ω     98.00 151.35   0.55    5.00    --  115.25  45.00  30.00   97
128  ω     97.00 131.10   0.55    5.00    --  115.25  61.00  60.00   62
129  ω    145.00 171.40   0.55    5.00    --  115.25  61.00-120.00   48
130  ω     96.00 140.00   0.55    5.00    --  115.25  61.00-120.00   80
131  ω     43.00  69.40   0.55    5.00    --  115.25 -77.00  30.00   48
132  ω     89.00 115.40   0.55    5.00    --  115.25 -81.00 121.16   48
133  ω     43.00  69.40   0.55    5.00    --  115.25 -77.00 -90.00   48
134  ω     92.00 124.45   0.55    5.00    --  115.25  77.00 150.00   59
135  ω     74.00 103.70   0.55    5.00    --  115.25 -77.00  60.00   54
136  ω    108.00 158.05   0.55    5.00    --  115.25 125.00 -60.00   91
137  ω     43.00  69.40   0.55    5.00    --  115.25 -77.00  60.00   48
138  ω    151.00 176.30   0.55    5.00    --  115.25  45.00-180.00   46
139  ω     99.00 161.15   0.55    5.00    --  115.25  61.00  30.00  113
140  ω    130.00 159.70   0.55    5.00    --  115.25  61.00-150.00   54
141  ω     44.00  98.45   0.55    5.00    --  115.25 -77.00 -60.00   99
142  ω     99.00 123.75   0.55    5.00    --  115.25  61.00-150.00   45
143  ω    142.00 174.45   0.55    5.00    --  115.25  30.00  60.00   59
144  ω    134.00 177.45   0.55    5.00    --  115.25  77.00-150.00   79
145  ω    111.00 137.40   0.55    5.00    --  115.25  45.00  60.00   48
146  ω    105.00 131.40   0.55    5.00    --  115.25  45.00   0.00   48
147  ω    129.00 155.40   0.55    5.00    --  115.25  45.00-120.00   48
148  ω     46.00  72.40   0.55    5.00    --  115.25-125.00  30.00   48
149  ω    136.00 173.40   0.55    5.00    --  115.25  45.00  90.00   68
150  ω     82.00 108.40   0.55    5.00    --  115.25-125.00-150.00   48
151  ω     44.00  70.40   0.55    5.00    --  115.25 -95.00 -30.00   48
152  ω     62.00  96.10   0.55    5.00    --  115.25 -95.00 -60.00   62
153  ω     66.00 102.30   0.55    5.00    --  115.25 -95.00-180.00   66
154  ω     73.00 102.70   0.55    5.00    --  115.25 -77.00-120.00   54
155  ω     45.00  77.45   0.55    5.00    --  115.25-125.00-150.00   59
156  ω     89.00 120.35   0.55    5.00    --  115.25  77.00-150.00   57
157  ω    147.00 176.70   0.55    5.00    --  115.25  45.00 -90.00   54
158  ω     44.00  68.75   0.55    5.00    --  115.25 -77.00  90.00   45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1032577000
_diffrn_orient_matrix_UB_12      0.1232054000
_diffrn_orient_matrix_UB_13      0.0626628000
_diffrn_orient_matrix_UB_21      0.0223279000
_diffrn_orient_matrix_UB_22      0.1492532000
_diffrn_orient_matrix_UB_23      -0.1287889000
_diffrn_orient_matrix_UB_31      -0.2010828000
_diffrn_orient_matrix_UB_32      0.0054979000
_diffrn_orient_matrix_UB_33      -0.0533711000
_diffrn_oxdiff_digest_hkl        
;
43cc2be48c49d133b0e6e725f673fed6c2a307
;
_diffrn_oxdiff_digest_od_ed      
;

;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2544
_reflns_number_total             2641
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.44.112a (Rigaku OD, 2025)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.143a 64-bit (release 25-10-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.44.112a (Rigaku OD, 2025)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.5-beta (Bourhis et al., 2015)'
_refine_diff_density_max         0.795
_refine_diff_density_min         -0.733
_refine_diff_density_rms         0.112
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2641
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0458
_refine_ls_restrained_S_all      1.106
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0967P)²+0.2224P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1293
_refine_ls_wR_factor_ref         0.1302
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
K1 K 0.62615(6) 0.42611(5) 0.22477(4) 0.02285(17) Uani 1 1 d . . . . .
N2 N 0.4308(3) 0.1983(2) 0.14259(18) 0.0279(4) Uani 1 1 d . . . . .
N3 N 0.3850(3) 0.2714(2) 0.01198(19) 0.0306(4) Uani 1 1 d . . . . .
N4 N 0.1965(3) 0.2996(2) -0.01143(18) 0.0276(4) Uani 1 1 d . . . . .
N5 N 0.1144(3) 0.2437(2) 0.10749(18) 0.0249(4) Uani 1 1 d . . . . .
O6 O -0.0744(2) 0.25063(19) 0.11990(15) 0.0277(3) Uani 1 1 d . . . . .
C7 C 0.2578(3) 0.1809(2) 0.2014(2) 0.0242(4) Uani 1 1 d . . . . .
C8 C 0.2293(3) 0.1098(2) 0.34292(19) 0.0217(4) Uani 1 1 d . . . . .
N9 N 0.1065(2) 0.1967(2) 0.40085(17) 0.0224(4) Uani 1 1 d . . . . .
O10 O -0.0044(2) 0.33855(19) 0.36099(16) 0.0273(3) Uani 1 1 d . . . . .
O11 O 0.1188(2) 0.09605(18) 0.54015(14) 0.0247(3) Uani 1 1 d . . . . .
N12 N 0.2565(2) -0.0549(2) 0.56231(17) 0.0229(4) Uani 1 1 d . . . . .
C13 C 0.3206(3) -0.0467(2) 0.44580(19) 0.0206(4) Uani 1 1 d . . . . .
C14 C 0.4670(3) -0.1855(2) 0.43222(19) 0.0210(4) Uani 1 1 d . . . . .
N15 N 0.5094(3) -0.1912(2) 0.31423(17) 0.0233(4) Uani 1 1 d . . . . .
N16 N 0.6542(3) -0.3372(2) 0.34085(18) 0.0252(4) Uani 1 1 d . . . . .
C17 C 0.6837(3) -0.4049(3) 0.4726(2) 0.0243(4) Uani 1 1 d . . . . .
H17 H 0.775(4) -0.500(4) 0.514(3) 0.026(6) Uiso 1 1 d . . . . .
N18 N 0.5702(2) -0.3164(2) 0.53612(17) 0.0232(4) Uani 1 1 d . . . . .
K19 K -0.19881(6) -0.03808(5) 0.15005(4) 0.02708(17) Uani 1 1 d . . . . .
O20 O 0.2047(2) -0.1156(2) 0.12522(16) 0.0282(3) Uani 1 1 d . . . . .
H20A H 0.217(6) -0.208(5) 0.124(4) 0.053(10) Uiso 1 1 d . . . . .
H20B H 0.296(6) -0.125(4) 0.179(4) 0.045(9) Uiso 1 1 d . . . . .
O21 O -0.2292(2) 0.4390(2) -0.14204(18) 0.0319(4) Uani 1 1 d . . . . .
H21A H -0.161(6) 0.392(5) -0.054(4) 0.056(10) Uiso 1 1 d . . . . .
H21B H -0.140(6) 0.471(5) -0.195(4) 0.059(11) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
K1 K1 4.9059(8) 2_665 ?
K1 N2 3.134(2) . ?
K1 N3 2.896(2) 2_665 ?
K1 N4 3.0940(18) 2_665 ?
K1 O6 2.7825(16) 1_655 ?
K1 O10 2.8465(16) 1_655 ?
K1 N12 3.1413(17) 2_656 ?
K1 N16 2.9247(19) 1_565 ?
K1 N18 2.8141(17) 2_656 ?
K1 K19 4.4223(6) 1_655 ?
K1 K19 4.9709(6) 1_665 ?
K1 O21 2.7933(17) 2_565 ?
N2 N3 1.342(3) . ?
N2 C7 1.350(3) . ?
N2 K19 2.9014(19) 1_655 ?
N3 N4 1.303(3) . ?
N3 K19 3.422(2) 1_655 ?
N4 N5 1.348(2) . ?
N4 K19 3.262(2) 2 ?
N5 O6 1.309(2) . ?
N5 C7 1.335(3) . ?
O6 K19 2.8116(16) . ?
C7 C8 1.449(3) . ?
C8 N9 1.324(3) . ?
C8 C13 1.427(3) . ?
N9 O10 1.234(2) . ?
N9 O11 1.429(2) . ?
O11 N12 1.394(2) . ?
O11 K19 3.3010(15) 2_556 ?
N12 C13 1.312(3) . ?
C13 C14 1.457(3) . ?
C14 N15 1.333(3) . ?
C14 N18 1.348(2) . ?
N15 N16 1.380(2) . ?
N15 K19 2.8684(18) 1_655 ?
N16 C17 1.337(3) . ?
N16 K19 3.0321(18) 1_655 ?
C17 H17 0.90(3) . ?
C17 N18 1.348(3) . ?
K19 K19 4.1353(8) 2 ?
K19 O20 2.7794(17) 2 ?
K19 O20 2.7624(17) . ?
K19 H20A 2.99(4) . ?
O20 H20A 0.82(4) . ?
O20 H20B 0.87(4) . ?
O21 H21A 0.99(4) . ?
O21 H21B 0.84(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
K1 K1 K19 98.612(12) 2_665 1_665 ?
N2 K1 K1 55.47(3) . 2_665 ?
N2 K1 N12 70.64(5) . 2_656 ?
N2 K1 K19 153.62(4) . 1_665 ?
N2 K1 K19 40.87(3) . 1_655 ?
N3 K1 K1 50.75(4) 2_665 2_665 ?
N3 K1 N2 106.20(5) 2_665 . ?
N3 K1 N4 24.85(5) 2_665 2_665 ?
N3 K1 N12 162.71(5) 2_665 2_656 ?
N3 K1 N16 79.09(5) 2_665 1_565 ?
N3 K1 K19 113.20(4) 2_665 1_655 ?
N3 K1 K19 48.00(4) 2_665 1_665 ?
N4 K1 K1 67.58(4) 2_665 2_665 ?
N4 K1 N2 119.94(5) 2_665 . ?
N4 K1 N12 141.94(5) 2_665 2_656 ?
N4 K1 K19 108.74(4) 2_665 1_655 ?
N4 K1 K19 39.78(4) 2_665 1_665 ?
O6 K1 K1 76.12(3) 1_655 2_665 ?
O6 K1 N2 74.33(5) 1_655 . ?
O6 K1 N3 89.55(5) 1_655 2_665 ?
O6 K1 N4 75.29(5) 1_655 2_665 ?
O6 K1 O10 68.07(5) 1_655 1_655 ?
O6 K1 N12 73.19(4) 1_655 2_656 ?
O6 K1 N16 128.05(5) 1_655 1_565 ?
O6 K1 N18 130.80(5) 1_655 2_656 ?
O6 K1 K19 38.00(3) 1_655 1_655 ?
O6 K1 K19 106.50(3) 1_655 1_665 ?
O6 K1 O21 129.01(5) 1_655 2_565 ?
O10 K1 K1 138.54(4) 1_655 2_665 ?
O10 K1 N2 128.30(5) 1_655 . ?
O10 K1 N3 107.62(5) 1_655 2_665 ?
O10 K1 N4 83.35(5) 1_655 2_665 ?
O10 K1 N12 65.45(4) 1_655 2_656 ?
O10 K1 N16 67.74(5) 1_655 1_565 ?
O10 K1 K19 73.24(3) 1_655 1_665 ?
O10 K1 K19 89.61(3) 1_655 1_655 ?
N12 K1 K1 123.17(4) 2_656 2_665 ?
N12 K1 K19 135.47(3) 2_656 1_665 ?
N12 K1 K19 52.93(3) 2_656 1_655 ?
N16 K1 K1 126.05(4) 1_565 2_665 ?
N16 K1 N2 157.49(5) 1_565 . ?
N16 K1 N4 73.82(5) 1_565 2_665 ?
N16 K1 N12 110.55(5) 1_565 2_656 ?
N16 K1 K19 156.99(4) 1_565 1_655 ?
N16 K1 K19 34.13(4) 1_565 1_665 ?
N18 K1 K1 127.72(4) 2_656 2_665 ?
N18 K1 N2 86.34(5) 2_656 . ?
N18 K1 N3 139.59(5) 2_656 2_665 ?
N18 K1 N4 149.43(5) 2_656 2_665 ?
N18 K1 O10 92.24(5) 2_656 1_655 ?
N18 K1 N12 57.70(5) 2_656 2_656 ?
N18 K1 N16 76.52(5) 2_656 1_565 ?
N18 K1 K19 110.04(4) 2_656 1_665 ?
N18 K1 K19 101.44(4) 2_656 1_655 ?
K19 K1 K1 73.627(12) 1_655 2_665 ?
K19 K1 K19 144.358(13) 1_655 1_665 ?
O21 K1 K1 55.96(4) 2_565 2_665 ?
O21 K1 N2 65.16(5) 2_565 . ?
O21 K1 N3 74.15(5) 2_565 2_665 ?
O21 K1 N4 98.90(5) 2_565 2_665 ?
O21 K1 O10 162.86(5) 2_565 1_655 ?
O21 K1 N12 117.43(5) 2_565 2_656 ?
O21 K1 N16 96.42(5) 2_565 1_565 ?
O21 K1 N18 77.13(5) 2_565 2_656 ?
O21 K1 K19 105.53(4) 2_565 1_655 ?
O21 K1 K19 97.55(3) 2_565 1_665 ?
N3 N2 K1 109.82(13) . . ?
N3 N2 C7 105.10(18) . . ?
N3 N2 K19 101.05(13) . 1_655 ?
C7 N2 K1 111.89(13) . . ?
C7 N2 K19 133.31(13) . 1_655 ?
K19 N2 K1 94.14(6) 1_655 . ?
K1 N3 K19 124.74(6) 2_665 1_655 ?
N2 N3 K1 143.81(15) . 2_665 ?
N2 N3 K19 56.32(11) . 1_655 ?
N4 N3 K1 86.11(12) . 2_665 ?
N4 N3 N2 111.42(18) . . ?
N4 N3 K19 143.74(14) . 1_655 ?
K1 N4 K19 102.86(5) 2_665 2 ?
N3 N4 K1 69.05(11) . 2_665 ?
N3 N4 N5 106.73(17) . . ?
N3 N4 K19 100.10(13) . 2 ?
N5 N4 K1 148.78(14) . 2_665 ?
N5 N4 K19 108.29(12) . 2 ?
O6 N5 N4 122.67(17) . . ?
O6 N5 C7 129.24(18) . . ?
C7 N5 N4 108.07(17) . . ?
K1 O6 K19 104.47(5) 1_455 . ?
N5 O6 K1 133.15(12) . 1_455 ?
N5 O6 K19 117.23(11) . . ?
N2 C7 C8 126.3(2) . . ?
N5 C7 N2 108.68(18) . . ?
N5 C7 C8 125.0(2) . . ?
N9 C8 C7 121.35(18) . . ?
N9 C8 C13 106.66(17) . . ?
C13 C8 C7 131.90(18) . . ?
C8 N9 O11 107.81(15) . . ?
O10 N9 C8 134.33(18) . . ?
O10 N9 O11 117.84(16) . . ?
N9 O10 K1 123.82(12) . 1_455 ?
N9 O11 K19 151.26(11) . 2_556 ?
N12 O11 N9 107.77(14) . . ?
N12 O11 K19 88.98(10) . 2_556 ?
O11 N12 K1 140.06(11) . 2_656 ?
C13 N12 K1 110.62(12) . 2_656 ?
C13 N12 O11 106.60(15) . . ?
C8 C13 C14 127.58(18) . . ?
N12 C13 C8 111.16(17) . . ?
N12 C13 C14 121.26(17) . . ?
N15 C14 C13 121.80(18) . . ?
N15 C14 N18 114.90(17) . . ?
N18 C14 C13 123.30(17) . . ?
C14 N15 N16 105.05(16) . . ?
C14 N15 K19 123.04(13) . 1_655 ?
N16 N15 K19 83.19(11) . 1_655 ?
K1 N16 K19 113.11(6) 1_545 1_655 ?
N15 N16 K1 120.84(13) . 1_545 ?
N15 N16 K19 69.94(10) . 1_655 ?
C17 N16 K1 114.92(13) . 1_545 ?
C17 N16 N15 104.90(16) . . ?
C17 N16 K19 125.26(14) . 1_655 ?
N16 C17 H17 121.6(18) . . ?
N16 C17 N18 114.83(18) . . ?
N18 C17 H17 123.5(18) . . ?
C14 N18 K1 116.99(12) . 2_656 ?
C17 N18 K1 130.27(13) . 2_656 ?
C17 N18 C14 100.32(17) . . ?
K1 K19 K1 144.358(13) 1_455 1_445 ?
K1 K19 H20A 124.8(8) 1_455 . ?
K1 K19 H20A 87.0(8) 1_445 . ?
N2 K19 K1 44.98(4) 1_455 1_455 ?
N2 K19 K1 105.72(4) 1_455 1_445 ?
N2 K19 N3 22.63(5) 1_455 1_455 ?
N2 K19 N4 117.37(5) 1_455 2 ?
N2 K19 O11 89.13(5) 1_455 2_556 ?
N2 K19 N16 93.06(5) 1_455 1_455 ?
N2 K19 K19 124.56(4) 1_455 2 ?
N2 K19 H20A 166.5(8) 1_455 . ?
N3 K19 K1 105.62(4) 1_455 1_445 ?
N3 K19 K1 56.30(4) 1_455 1_455 ?
N3 K19 K19 104.54(3) 1_455 2 ?
N3 K19 H20A 149.5(7) 1_455 . ?
N4 K19 K1 37.36(3) 2 1_445 ?
N4 K19 K1 159.01(4) 2 1_455 ?
N4 K19 N3 103.09(5) 2 1_455 ?
N4 K19 O11 132.22(4) 2 2_556 ?
N4 K19 K19 71.27(3) 2 2 ?
N4 K19 H20A 70.2(8) 2 . ?
O6 K19 K1 37.53(3) . 1_455 ?
O6 K19 K1 175.73(4) . 1_445 ?
O6 K19 N2 77.73(5) . 1_455 ?
O6 K19 N3 78.54(5) . 1_455 ?
O6 K19 N4 143.32(5) . 2 ?
O6 K19 O11 77.36(4) . 2_556 ?
O6 K19 N15 131.00(5) . 1_455 ?
O6 K19 N16 145.77(5) . 1_455 ?
O6 K19 K19 72.89(3) . 2 ?
O6 K19 H20A 89.8(8) . . ?
O11 K19 K1 99.99(3) 2_556 1_445 ?
O11 K19 K1 65.88(3) 2_556 1_455 ?
O11 K19 N3 111.14(4) 2_556 1_455 ?
O11 K19 K19 127.10(3) 2_556 2 ?
O11 K19 H20A 93.2(8) 2_556 . ?
N15 K19 K1 49.98(3) 1_455 1_445 ?
N15 K19 K1 94.68(4) 1_455 1_455 ?
N15 K19 N2 66.20(5) 1_455 1_455 ?
N15 K19 N3 79.97(5) 1_455 1_455 ?
N15 K19 N4 84.45(5) 1_455 2 ?
N15 K19 O11 70.33(5) 1_455 2_556 ?
N15 K19 N16 26.87(5) 1_455 1_455 ?
N15 K19 K19 155.72(4) 1_455 2 ?
N15 K19 H20A 127.0(8) 1_455 . ?
N16 K19 K1 116.39(4) 1_455 1_455 ?
N16 K19 K1 32.76(3) 1_455 1_445 ?
N16 K19 N3 105.22(5) 1_455 1_455 ?
N16 K19 N4 70.04(5) 1_455 2 ?
N16 K19 O11 69.51(4) 1_455 2_556 ?
N16 K19 K19 135.31(4) 1_455 2 ?
N16 K19 H20A 100.2(8) 1_455 . ?
K19 K19 K1 107.756(16) 2 1_455 ?
K19 K19 K1 106.586(16) 2 1_445 ?
K19 K19 H20A 45.0(7) 2 . ?
O20 K19 K1 97.25(4) 2 1_455 ?
O20 K19 K1 109.24(4) . 1_455 ?
O20 K19 K1 102.54(4) . 1_445 ?
O20 K19 K1 102.06(4) 2 1_445 ?
O20 K19 N2 88.25(5) 2 1_455 ?
O20 K19 N2 151.63(5) . 1_455 ?
O20 K19 N3 65.92(5) 2 1_455 ?
O20 K19 N3 141.84(5) . 1_455 ?
O20 K19 N4 84.34(5) . 2 ?
O20 K19 N4 67.69(5) 2 2 ?
O20 K19 O6 74.16(5) . . ?
O20 K19 O6 80.42(5) 2 . ?
O20 K19 O11 88.41(4) . 2_556 ?
O20 K19 O11 157.67(5) 2 2_556 ?
O20 K19 N15 127.99(5) 2 1_455 ?
O20 K19 N15 138.19(5) . 1_455 ?
O20 K19 N16 132.77(5) 2 1_455 ?
O20 K19 N16 112.40(5) . 1_455 ?
O20 K19 K19 41.58(3) 2 2 ?
O20 K19 K19 41.89(3) . 2 ?
O20 K19 O20 83.48(5) . 2 ?
O20 K19 H20A 15.7(8) . . ?
O20 K19 H20A 84.5(7) 2 . ?
K19 O20 K19 96.52(5) . 2 ?
K19 O20 H20A 92(3) 2 . ?
K19 O20 H20A 98(3) . . ?
K19 O20 H20B 128(2) . . ?
K19 O20 H20B 126(2) 2 . ?
H20A O20 H20B 107(4) . . ?
K1 O21 H21A 133(2) 2_565 . ?
K1 O21 H21B 120(3) 2_565 . ?
H21A O21 H21B 103(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O20 H20B N15 0.87(4) 1.98(4) 2.839(2) 169(3) . yes
O21 H21A N4 0.99(4) 2.45(4) 3.128(3) 126(3) . yes
O21 H21A N5 0.99(4) 2.44(4) 3.363(3) 157(3) . yes
O21 H21A O6 0.99(4) 1.86(4) 2.817(2) 162(3) . yes
O21 H21B O10 0.84(4) 2.32(4) 3.112(2) 156(4) 2_565 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
K1 N2 N3 K1 -5.9(3) . . . 2_665 ?
K1 N2 N3 N4 -120.24(16) . . . . ?
K1 N2 N3 K19 98.55(10) . . . 1_655 ?
K1 N2 C7 N5 118.57(15) . . . . ?
K1 N2 C7 C8 -60.1(2) . . . . ?
K1 N3 N4 N5 -147.26(14) 2_665 . . . ?
K1 N3 N4 K19 100.01(6) 2_665 . . 2 ?
K1 N4 N5 O6 104.1(3) 2_665 . . . ?
K1 N4 N5 C7 -77.5(3) 2_665 . . . ?
K1 N12 C13 C8 165.77(12) 2_656 . . . ?
K1 N12 C13 C14 -14.4(2) 2_656 . . . ?
K1 N16 C17 N18 -134.91(15) 1_545 . . . ?
N2 N3 N4 K1 147.38(18) . . . 2_665 ?
N2 N3 N4 N5 0.1(2) . . . . ?
N2 N3 N4 K19 -112.61(16) . . . 2 ?
N2 C7 C8 N9 122.7(2) . . . . ?
N2 C7 C8 C13 -53.4(3) . . . . ?
N3 N2 C7 N5 -0.6(2) . . . . ?
N3 N2 C7 C8 -179.19(19) . . . . ?
N3 N4 N5 O6 -178.91(18) . . . . ?
N3 N4 N5 C7 -0.5(2) . . . . ?
N4 N5 O6 K1 -114.73(19) . . . 1_455 ?
N4 N5 O6 K19 95.10(19) . . . . ?
N4 N5 C7 N2 0.6(2) . . . . ?
N4 N5 C7 C8 179.30(18) . . . . ?
N5 C7 C8 N9 -55.7(3) . . . . ?
N5 C7 C8 C13 128.1(2) . . . . ?
O6 N5 C7 N2 178.95(18) . . . . ?
O6 N5 C7 C8 -2.4(3) . . . . ?
C7 N2 N3 K1 114.6(2) . . . 2_665 ?
C7 N2 N3 N4 0.3(2) . . . . ?
C7 N2 N3 K19 -140.95(18) . . . 1_655 ?
C7 N5 O6 K1 67.2(3) . . . 1_455 ?
C7 N5 O6 K19 -83.0(2) . . . . ?
C7 C8 N9 O10 0.9(4) . . . . ?
C7 C8 N9 O11 -177.14(17) . . . . ?
C7 C8 C13 N12 176.3(2) . . . . ?
C7 C8 C13 C14 -3.5(4) . . . . ?
C8 N9 O10 K1 76.2(3) . . . 1_455 ?
C8 N9 O11 N12 0.4(2) . . . . ?
C8 N9 O11 K19 123.5(2) . . . 2_556 ?
C8 C13 C14 N15 -11.5(3) . . . . ?
C8 C13 C14 N18 168.13(19) . . . . ?
N9 C8 C13 N12 -0.3(2) . . . . ?
N9 C8 C13 C14 179.94(19) . . . . ?
N9 O11 N12 K1 -158.79(14) . . . 2_656 ?
N9 O11 N12 C13 -0.59(19) . . . . ?
O10 N9 O11 N12 -177.94(16) . . . . ?
O10 N9 O11 K19 -54.9(3) . . . 2_556 ?
O11 N9 O10 K1 -105.94(16) . . . 1_455 ?
O11 N12 C13 C8 0.5(2) . . . . ?
O11 N12 C13 C14 -179.65(17) . . . . ?
N12 C13 C14 N15 168.74(18) . . . . ?
N12 C13 C14 N18 -11.7(3) . . . . ?
C13 C8 N9 O10 177.9(2) . . . . ?
C13 C8 N9 O11 -0.1(2) . . . . ?
C13 C14 N15 N16 179.14(18) . . . . ?
C13 C14 N15 K19 87.5(2) . . . 1_655 ?
C13 C14 N18 K1 34.9(2) . . . 2_656 ?
C13 C14 N18 C17 -179.04(18) . . . . ?
C14 N15 N16 K1 131.97(13) . . . 1_545 ?
C14 N15 N16 C17 0.2(2) . . . . ?
C14 N15 N16 K19 -122.44(14) . . . 1_655 ?
N15 C14 N18 K1 -145.52(14) . . . 2_656 ?
N15 C14 N18 C17 0.6(2) . . . . ?
N15 N16 C17 N18 0.2(2) . . . . ?
N16 C17 N18 K1 138.88(16) . . . 2_656 ?
N16 C17 N18 C14 -0.5(2) . . . . ?
N18 C14 N15 N16 -0.5(2) . . . . ?
N18 C14 N15 K19 -92.12(18) . . . 1_655 ?
K19 N2 N3 K1 -104.4(2) 1_655 . . 2_665 ?
K19 N2 N3 N4 141.22(15) 1_655 . . . ?
K19 N2 C7 N5 -122.37(18) 1_655 . . . ?
K19 N2 C7 C8 59.0(3) 1_655 . . . ?
K19 N3 N4 K1 -150.8(2) 1_655 . . 2_665 ?
K19 N3 N4 N5 61.9(3) 1_655 . . . ?
K19 N3 N4 K19 -50.8(2) 1_655 . . 2 ?
K19 N4 N5 O6 -71.92(19) 2 . . . ?
K19 N4 N5 C7 106.52(15) 2 . . . ?
K19 O11 N12 K1 44.98(16) 2_556 . . 2_656 ?
K19 O11 N12 C13 -156.82(13) 2_556 . . . ?
K19 N15 N16 K1 -105.58(10) 1_655 . . 1_545 ?
K19 N15 N16 C17 122.60(14) 1_655 . . . ?
K19 N16 C17 N18 75.9(2) 1_655 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.568
_oxdiff_exptl_absorpt_empirical_full_min 0.652
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Ris570c
_database_code_depnum_ccdc_archive 'CCDC 2492510'
loop_
_audit_author_name
_audit_author_address
'Dmitry Vinogradov'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2025-10-01 deposited with the CCDC.	2025-11-26 downloaded from the CCDC.
;
_audit_creation_date             2024-09-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 H3 N9 O3'
_chemical_formula_sum            'C5 H3 N9 O3'
_chemical_formula_weight         237.16
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C5 H3 N9 O3'
_chemical_oxdiff_usercomment     Ris570.C
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   18.3967(3)
_cell_length_b                   7.17590(10)
_cell_length_c                   13.5983(2)
_cell_angle_alpha                90
_cell_angle_beta                 110.355(2)
_cell_angle_gamma                90
_cell_volume                     1683.05(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6280
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      78.9880
_cell_measurement_theta_min      3.4300
_shelx_estimated_absorpt_T_max   0.921
_shelx_estimated_absorpt_T_min   0.862
_exptl_absorpt_coefficient_mu    1.388
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.735
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.136a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.872
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             960
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.0095
1 1 2 0.0520
0 -1 2 0.0477
0 1 -2 0.0438
-1 1 1 0.0497
-1 0 2 0.0530
1 0 -2 0.0474
-2 -1 2 0.0568
1 1 -1 0.0569
1 -2 -2 0.0468
-2 0 1 0.0474
-11 2 2 0.0329
-10 1 -1 0.0418

_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0000 0.0000 0.0000 -0.0860 -0.0228 -0.0078
1.0000 1.0000 2.0000 -0.1958 -0.0414 0.2956
-0.0000 -1.0000 2.0000 -0.1616 0.2800 -0.0008
0.0000 1.0000 -2.0000 0.1616 -0.2800 0.0008
-1.0000 1.0000 1.0000 0.0440 -0.0611 0.2355
-1.0000 0.0000 2.0000 -0.0497 0.1535 0.1591
1.0000 -0.0000 -2.0000 0.0497 -0.1535 -0.1591
-2.0000 -1.0000 2.0000 0.0105 0.3256 0.0148
1.0000 1.0000 -1.0000 0.0077 -0.2375 0.0686
1.0000 -2.0000 -2.0000 -0.0021 0.1451 -0.4633
-2.0000 0.0000 1.0000 0.1042 0.1110 0.0913
-10.6208 2.0946 2.0644 0.8276 0.0644 0.5576
-10.4685 0.5608 -1.1622 0.9937 0.0791 0.0790

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9651
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.832
_diffrn_reflns_theta_min         5.129
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -64.00  28.40   0.55    0.50    --  -44.86  60.00 169.00  168
  2  ω    -64.00  28.40   0.55    0.50    --  -44.86  60.00 169.00  168
  3  ω   -117.00 -26.80   0.55    0.50    --  -44.86 -60.00  30.00  164
  4  ω    -70.00 -21.05   0.55    2.00    --  -93.75  60.00 169.00   89
  5  ω   -167.00 -74.60   0.55    2.00    --  -93.75 -60.00  30.00  168
  6  ω     96.00 177.40   0.55    2.00    --  115.25  60.00 169.00  148
  7  ω     43.00  68.85   0.55    2.00    --  115.25 -60.00  30.00   47
  8  ω    -27.00  63.20   0.55    0.50    --   44.86 -60.00  30.00  164
  9  ω     34.00  92.85   0.55    0.50    --   44.86-125.00-120.00  107
 10  ω     34.00  92.85   0.55    0.50    --   44.86-125.00   0.00  107
 11  ω    -51.00 -20.75   0.55    2.00    --  -93.75  45.00   0.00   55
 12  ω     97.00 177.30   0.55    2.00    --  115.25  45.00 120.00  146
 13  ω     97.00 177.30   0.55    2.00    --  115.25  45.00 120.00  146
 14  ω     97.00 177.30   0.55    2.00    --  115.25  45.00  90.00  146
 15  ω     43.00 103.50   0.55    2.00    --  115.25 -77.00  30.00  110
 16  ω     43.00  69.95   0.55    2.00    --  115.25 -61.00 -30.00   49
 17  ω     43.00  69.95   0.55    2.00    --  115.25 -61.00 120.00   49
 18  ω     99.00 157.30   0.55    2.00    --  115.25  61.00-120.00  106
 19  ω     99.00 157.30   0.55    2.00    --  115.25  61.00-120.00  106
 20  ω     43.00 104.05   0.55    2.00    --  115.25 -95.00  30.00  111
 21  ω     52.00  88.30   0.55    2.00    --  115.25-125.00 -30.00   66
 22  ω     44.00  92.40   0.55    2.00    --  115.25 -77.00  90.00   88
 23  ω     73.00 100.50   0.55    2.00    --  115.25 -77.00 -30.00   50
 24  ω     58.00 105.30   0.55    2.00    --  115.25-125.00-120.00   86
 25  ω    125.00 173.40   0.55    2.00    --  115.25  61.00 -90.00   88
 26  ω     44.00  68.75   0.55    2.00    --  115.25 -61.00 150.00   45
 27  ω     97.00 162.45   0.55    2.00    --  115.25  45.00 -30.00  119
 28  ω    119.00 145.40   0.55    2.00    --  115.25  45.00  60.00   48
 29  ω    147.00 172.30   0.55    2.00    --  115.25  45.00  60.00   46
 30  ω     45.00  71.40   0.55    2.00    --  115.25 -77.00 -30.00   48
 31  ω     57.00 100.45   0.55    2.00    --  115.25 -77.00-120.00   79
 32  ω     50.00  76.40   0.55    2.00    --  115.25 -95.00  90.00   48
 33  ω     70.00 107.40   0.55    2.00    --  115.25-125.00-180.00   68
 34  ω    122.00 147.30   0.55    2.00    --  115.25  45.00-150.00   46
 35  ω    113.00 163.05   0.55    2.00    --  115.25  45.00 -90.00   91
 36  ω    101.00 127.40   0.55    2.00    --  115.25  77.00 -30.00   48
 37  ω     43.00  67.75   0.55    2.00    --  115.25 -61.00 -60.00   45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0860089000
_diffrn_orient_matrix_UB_12      0.0258762000
_diffrn_orient_matrix_UB_13      -0.0678403000
_diffrn_orient_matrix_UB_21      -0.0228094000
_diffrn_orient_matrix_UB_22      -0.1493121000
_diffrn_orient_matrix_UB_23      0.0653586000
_diffrn_orient_matrix_UB_31      -0.0077950000
_diffrn_orient_matrix_UB_32      0.1520925000
_diffrn_orient_matrix_UB_33      0.0756623000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1690
_reflns_number_total             1837
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.136a 64-bit (release 23-08-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         1837
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0320
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0471P)²+1.6156P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.0889
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.56054(5) 0.84575(13) 0.68693(7) 0.0196(2) Uani 1 1 d . . . . .
N2 N 0.61870(6) 0.81281(15) 0.66713(8) 0.0154(2) Uani 1 1 d . . . . .
O3 O 0.67422(5) 0.96445(13) 0.67783(7) 0.0180(2) Uani 1 1 d . . . . .
N4 N 0.73588(6) 0.89375(15) 0.65463(8) 0.0173(2) Uani 1 1 d . . . . .
C5 C 0.72056(7) 0.71789(17) 0.62944(9) 0.0144(2) Uani 1 1 d . . . . .
C6 C 0.77690(7) 0.60304(17) 0.60375(9) 0.0144(2) Uani 1 1 d . . . . .
N7 N 0.76253(6) 0.42961(15) 0.56953(8) 0.0172(2) Uani 1 1 d . . . . .
N8 N 0.83158(6) 0.37727(16) 0.56248(9) 0.0175(2) Uani 1 1 d . . . . .
H8 H 0.8370(11) 0.271(3) 0.5367(15) 0.030(5) Uiso 1 1 d . . . . .
C9 C 0.88271(7) 0.51523(18) 0.59141(9) 0.0170(3) Uani 1 1 d . . . . .
H9 H 0.9324(11) 0.507(2) 0.5923(14) 0.021(4) Uiso 1 1 d . . . . .
N10 N 0.85020(6) 0.66361(15) 0.61794(8) 0.0156(2) Uani 1 1 d . . . . .
C11 C 0.64817(7) 0.66382(17) 0.63601(9) 0.0145(3) Uani 1 1 d . . . . .
C12 C 0.60490(7) 0.49075(18) 0.61650(9) 0.0154(3) Uani 1 1 d . . . . .
N13 N 0.57472(6) 0.41411(15) 0.68370(8) 0.0159(2) Uani 1 1 d . . . . .
O14 O 0.58463(5) 0.47166(13) 0.78264(7) 0.0189(2) Uani 1 1 d . . . . .
H14 H 0.6095(15) 0.357(4) 0.825(2) 0.062(7) Uiso 1 1 d . . . . .
N15 N 0.53310(6) 0.26446(16) 0.64022(9) 0.0197(2) Uani 1 1 d . . . . .
N16 N 0.53901(7) 0.24900(16) 0.54755(9) 0.0209(3) Uani 1 1 d . . . . .
N17 N 0.58321(6) 0.38904(16) 0.53006(9) 0.0190(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N2 1.2139(14) . ?
N2 O3 1.4646(14) . ?
N2 C11 1.3325(16) . ?
O3 N4 1.3756(14) . ?
N4 C5 1.3123(17) . ?
C5 C6 1.4586(17) . ?
C5 C11 1.4195(17) . ?
C6 N7 1.3227(16) . ?
C6 N10 1.3650(16) . ?
N7 N8 1.3597(15) . ?
N8 H8 0.86(2) . ?
N8 C9 1.3275(17) . ?
C9 H9 0.912(19) . ?
C9 N10 1.3312(17) . ?
C11 C12 1.4489(17) . ?
C12 N13 1.3412(16) . ?
C12 N17 1.3218(16) . ?
N13 O14 1.3577(14) . ?
N13 N15 1.3320(16) . ?
O14 H14 1.02(3) . ?
N15 N16 1.3066(16) . ?
N16 N17 1.3645(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N2 O3 118.12(10) . . ?
O1 N2 C11 135.56(11) . . ?
C11 N2 O3 106.32(10) . . ?
N4 O3 N2 107.78(8) . . ?
C5 N4 O3 107.17(10) . . ?
N4 C5 C6 119.99(11) . . ?
N4 C5 C11 111.56(11) . . ?
C11 C5 C6 128.40(12) . . ?
N7 C6 C5 122.96(11) . . ?
N7 C6 N10 114.59(11) . . ?
N10 C6 C5 122.38(11) . . ?
C6 N7 N8 101.97(10) . . ?
N7 N8 H8 121.2(13) . . ?
C9 N8 N7 110.87(11) . . ?
C9 N8 H8 127.7(13) . . ?
N8 C9 H9 124.0(11) . . ?
N8 C9 N10 109.75(11) . . ?
N10 C9 H9 126.2(11) . . ?
C9 N10 C6 102.82(10) . . ?
N2 C11 C5 107.15(11) . . ?
N2 C11 C12 119.19(11) . . ?
C5 C11 C12 133.66(11) . . ?
N13 C12 C11 123.92(11) . . ?
N17 C12 C11 127.79(11) . . ?
N17 C12 N13 108.12(11) . . ?
C12 N13 O14 127.28(11) . . ?
N15 N13 C12 109.78(10) . . ?
N15 N13 O14 122.92(10) . . ?
N13 O14 H14 101.3(14) . . ?
N16 N15 N13 105.59(10) . . ?
N15 N16 N17 111.10(11) . . ?
C12 N17 N16 105.40(10) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N8 H8 N7 0.86(2) 2.38(2) 2.9845(15) 127.5(16) 7_656 yes
N8 H8 N17 0.86(2) 2.28(2) 3.0109(15) 142.1(17) 7_656 yes
C9 H9 O1 0.912(19) 2.538(19) 3.3034(16) 141.8(14) 3_545 yes
C9 H9 N15 0.912(19) 2.536(18) 3.1648(17) 126.5(14) 3 yes
O14 H14 N10 1.02(3) 1.64(3) 2.6502(14) 174(2) 4_646 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N2 O3 N4 178.22(10) . . . . ?
O1 N2 C11 C5 -178.59(13) . . . . ?
O1 N2 C11 C12 1.4(2) . . . . ?
N2 O3 N4 C5 1.36(12) . . . . ?
N2 C11 C12 N13 -49.56(17) . . . . ?
N2 C11 C12 N17 125.06(14) . . . . ?
O3 N2 C11 C5 1.22(12) . . . . ?
O3 N2 C11 C12 -178.77(10) . . . . ?
O3 N4 C5 C6 -178.12(10) . . . . ?
O3 N4 C5 C11 -0.63(13) . . . . ?
N4 C5 C6 N7 -174.31(11) . . . . ?
N4 C5 C6 N10 8.86(18) . . . . ?
N4 C5 C11 N2 -0.42(14) . . . . ?
N4 C5 C11 C12 179.56(12) . . . . ?
C5 C6 N7 N8 -176.60(11) . . . . ?
C5 C6 N10 C9 176.39(11) . . . . ?
C5 C11 C12 N13 130.46(14) . . . . ?
C5 C11 C12 N17 -54.9(2) . . . . ?
C6 C5 C11 N2 176.80(11) . . . . ?
C6 C5 C11 C12 -3.2(2) . . . . ?
C6 N7 N8 C9 -0.04(13) . . . . ?
N7 C6 N10 C9 -0.68(14) . . . . ?
N7 N8 C9 N10 -0.39(15) . . . . ?
N8 C9 N10 C6 0.62(14) . . . . ?
N10 C6 N7 N8 0.46(14) . . . . ?
C11 N2 O3 N4 -1.63(12) . . . . ?
C11 C5 C6 N7 8.67(19) . . . . ?
C11 C5 C6 N10 -168.16(11) . . . . ?
C11 C12 N13 O14 -6.52(19) . . . . ?
C11 C12 N13 N15 174.94(11) . . . . ?
C11 C12 N17 N16 -175.27(12) . . . . ?
C12 N13 N15 N16 0.90(14) . . . . ?
N13 C12 N17 N16 0.03(13) . . . . ?
N13 N15 N16 N17 -0.89(14) . . . . ?
O14 N13 N15 N16 -177.71(11) . . . . ?
N15 N16 N17 C12 0.55(14) . . . . ?
N17 C12 N13 O14 177.95(11) . . . . ?
N17 C12 N13 N15 -0.59(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.268
_oxdiff_exptl_absorpt_empirical_full_min 0.870
